Stable Langmuir and Langmuir-Blodgett films of Fullerene-Glycodendron conjugates

Langmuir

Volumn 14, Issue 8, 1998, Pages 1955-1959

  Cardullo, Francesca ^a   Diederich, François ^a   Echegoyen, Luis ^a,b   Habicher, Tilo ^a   Jayaraman, Narayanaswamy ^c   Leblanc, Roger M ^b   Stoddart, J Fraser ^c   Wang, Shaopeng ^b  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF MIAMI   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; COMPACTION; EXPANSION; FULLERENES; MOLECULAR STRUCTURE; MONOLAYERS; PHASE INTERFACES; QUARTZ; ULTRAVIOLET SPECTROSCOPY;

AMPHIPHILIC CONJUGATES; BREWSTER ANGLE MICROSCOPY; DENDRIMERS; GLYCODENDRON; LANGMUIR MONOLAYERS;

LANGMUIR BLODGETT FILMS;

EID: 0032050509     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la971221u     Document Type: Article

References (54)

1. Mirkin, C. A.; Caldwell, W. B. Tetrahedron 1996, 52, 5113.
2. Prato, M. J. Mater. Chem. 1997, 7, 1097.
3. Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537.
4. Jonas, U.; Cardullo, F.; Belik, P.; Diederich, F.; Gügel, A.; Harth, E.; Herrmann, A.; Isaacs, L.; Müllen, K.; Ringsdorf, H.; Thilgen, C.; Uhlmann, P.; Vasella, A.; Waldraff, C. A. A.; Walter, M. Chem. Eur. J. 1995, 1, 243 and references therein.
5. Haddon, R. C. Acc. Chem. Res. 1992, 25, 127.
6. (a) Hughes, R. C.; Ricco, A. J.; Butler, M. A.; Martin, S. J. Science 1991, 254, 74.
7. (b) Sun, R.; Li, Y.; Zheng, J.; Li, D.; Fan, Y.; Lu, A.; Zhang, X. Thin Solid Films 1994, 248, 100.
8. (c) Li, D.; Swanson, B. I. Langmuir 1993, 9, 3341.
9. (a) Baum, R. Chem. Eng. News 1994, November 7, 29.
10. (b) Janssen, R. A. J.; Christiaans, M. P. T.; Pakbaz, K.; Moses, D.; Hummelen, J. C.; Sariciftci, N. S. J. Chem. Phys. 1995, 102, 2628.
11. (c) Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789.
12. (a) Hoshi, H.; Nakamura N.; Maruyama, Y.; Nakagawa, T.; Suzuki, S.; Shiromaru, H.; Achiba, Y. Jpn. J. Appl. Phys. 1991, 30, L1397.
13. (b) Kazjar, F.; Taliani, C.; Zamboni, R.; Rossini, S.; Danieli, R. Synth. Met. 1993, 54, 21.
14. (c) Wang, X. K.; Zhang, T. G.; Lin, W. P.; Liu, S. Z.; Wong, G. K.; Kappes, M. M.; Chang, R. P. H.; Ketterson, J. B. Appl. Phys. Lett. 1992, 60, 810.
15. Heiney, P. A.; Fischer, J. E.; McGhie, A. R.; Romanow, W. J.; Denenstein, A. M.; McCauley, J. P., Jr.; Smith, A. B., III; Cox, D. E. Phys. Rev. Lett. 1991, 66, 2911.
16. (a) Jehoulet, C.; Obeng, Y. S.; Kim, Y.-T.; Zhou, F.; Bard, A. J. J. Am. Chem. Soc. 1992, 114, 4237.
17. (b) Obeng, Y. S.; Bard, A. J. J. Am. Chem. Soc. 1991, 113, 6279.
18. (c) Maliszewskyj, N. C.; Heiney, P. A.; Jones, D. R.; Strongin, R. M.; Cichy, M. A.; Smith, A. B., III Langmuir 1993, 9, 1439.
19. Diederich, F.; Jonas,U.; Gramlich, V.; Herrmann, A.; Ringsdorf, H.; Thilgen, C. Helv. Chim. Acta 1993, 76, 2445.
20. (a) Hawker, C. J.; Saville, P. M.; White, J. W. J. Org. Chem. 1994, 59, 3503.
21. (b) Maggini, M.; Karlsson, A.; Pasimeni, L.; Scorrano, G.; Prato, M.; Valli, L. Tetrahedron Lett. 1994, 35, 2985.
22. (c) Maggini, M.; Pasimeni, L.; Prato, M.; Scorrano, G.; Valli, L. Langmuir 1994, 10, 4164.
23. (d) Wang, J. Y.; Vaknin, D.; Uphaus, R. A.; Kjaer, K.; Lösche, M. Thin Solid Films 1994, 242, 40.
24. (e) Patel, H. M.; Didymus, J. M.; Wong, K. K. W.; Hirsch, A.; Skiebe, A.; Lamparth, I.; Mann, S. Chem. Commun. 1996, 611.
25. (f) Zhou, D.; Gan, L.; Luo, C.; Tan, H.; Huang, C.; Yao, G.; Zhao, X.; Liu, Z.; Xia, X.; Zhang, B. J. Phys. Chem. 1996, 100, 3150.
26. (g) Guldi, D. M.; Tian, Y.; Fendler, J. H.; Hungerbühler, H.; Asmus, K.-D. J. Phys. Chem. 1995, 99, 17673.
27. (h) Guldi, D. M.; Tian, Y.; Fendler, J. H.; Hungerbühler, H.; Asmus, K.-D. J. Phys. Chem. 1996, 100, 2753.
28. (i) Luo, C.; Huang, C.; Gan, L.; Zhou, D.; Xia, W.; Zhuang, Q.; Zhao, Y.; Huang, Y. J. Phys. Chem. 1996, 100, 16685.
29. Wang, S. P.; Leblanc, R. M.; Arias, F.; Echegoyen, L. Langmuir 1997, 13, 1672.
30. (a) Hamza, A. V.; Balooch, M. Chem. Phys. Lett. 1993, 201, 404.
31. (b) Hamza, A. V.; Balooch, M. Chem. Phys. Lett. 1992, 198, 603.
32. (c) Li, Y. Z.; Chander, M.; Patrin, J. C.; Weaver, J. H.; Chibante, L. P. F.; Smalley, R. E. Science 1991, 253, 429.
33. (d) Tokmakoff, A.; Haynes, D. R.; George, S. M. Chem. Phys. Lett. 1991, 186, 450.
34. (e) Shi, X.; Caldwell, W. B.; Chen, K.; Mirkin, C. A. J. Am. Chem. Soc. 1994, 116, 11598.
35. Leigh, D. A.; Moody, A. E.; Wade, F. A.; King, T. A.; West, D.; Bahra, G. S. Langmuir 1995, 11, 2334.
36. For fullerene - dendrimer conjugates see: (a) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J.; Wudl, F.; Srdanov, G.; Shi, S.; Li, C.; Kao, M. J. Am. Chem. Soc. 1993, 115, 9836. (b) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc., Chem. Commun. 1994, 925. (c) Camps, X.; Hirsch, A. J. Chem. Soc., Perkin Trans, 1 1997, 1595. (d) Camps, X.; Schönberger, H.; Hirsch, A. Chem. Eur. J. 1997, 3, 561. (e) Catalano, V. J.; Parodi, N. Inorg. Chem. 1997, 36, 537. (f) Nierengarten, J.-F.; Habicher, T.; Kessinger, R.; Cardullo, F.; Diederich, F.; Gramlich, V.; Gisselbrecht, J.-P.; Boudon, C.; Gross, M. Helv. Chim. Acta 1997, 80, 2238.
37. For fullerene - dendrimer conjugates see: (a) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J.; Wudl, F.; Srdanov, G.; Shi, S.; Li, C.; Kao, M. J. Am. Chem. Soc. 1993, 115, 9836. (b) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc., Chem. Commun. 1994, 925. (c) Camps, X.; Hirsch, A. J. Chem. Soc., Perkin Trans, 1 1997, 1595. (d) Camps, X.; Schönberger, H.; Hirsch, A. Chem. Eur. J. 1997, 3, 561. (e) Catalano, V. J.; Parodi, N. Inorg. Chem. 1997, 36, 537. (f) Nierengarten, J.-F.; Habicher, T.; Kessinger, R.; Cardullo, F.; Diederich, F.; Gramlich, V.; Gisselbrecht, J.-P.; Boudon, C.; Gross, M. Helv. Chim. Acta 1997, 80, 2238.
38. For fullerene - dendrimer conjugates see: (a) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J.; Wudl, F.; Srdanov, G.; Shi, S.; Li, C.; Kao, M. J. Am. Chem. Soc. 1993, 115, 9836. (b) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc., Chem. Commun. 1994, 925. (c) Camps, X.; Hirsch, A. J. Chem. Soc., Perkin Trans, 1 1997, 1595. (d) Camps, X.; Schönberger, H.; Hirsch, A. Chem. Eur. J. 1997, 3, 561. (e) Catalano, V. J.; Parodi, N. Inorg. Chem. 1997, 36, 537. (f) Nierengarten, J.-F.; Habicher, T.; Kessinger, R.; Cardullo, F.; Diederich, F.; Gramlich, V.; Gisselbrecht, J.-P.; Boudon, C.; Gross, M. Helv. Chim. Acta 1997, 80, 2238.
39. For fullerene - dendrimer conjugates see: (a) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J.; Wudl, F.; Srdanov, G.; Shi, S.; Li, C.; Kao, M. J. Am. Chem. Soc. 1993, 115, 9836. (b) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc., Chem. Commun. 1994, 925. (c) Camps, X.; Hirsch, A. J. Chem. Soc., Perkin Trans, 1 1997, 1595. (d) Camps, X.; Schönberger, H.; Hirsch, A. Chem. Eur. J. 1997, 3, 561. (e) Catalano, V. J.; Parodi, N. Inorg. Chem. 1997, 36, 537. (f) Nierengarten, J.-F.; Habicher, T.; Kessinger, R.; Cardullo, F.; Diederich, F.; Gramlich, V.; Gisselbrecht, J.-P.; Boudon, C.; Gross, M. Helv. Chim. Acta 1997, 80, 2238.
40. For fullerene - dendrimer conjugates see: (a) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J.; Wudl, F.; Srdanov, G.; Shi, S.; Li, C.; Kao, M. J. Am. Chem. Soc. 1993, 115, 9836. (b) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc., Chem. Commun. 1994, 925. (c) Camps, X.; Hirsch, A. J. Chem. Soc., Perkin Trans, 1 1997, 1595. (d) Camps, X.; Schönberger, H.; Hirsch, A. Chem. Eur. J. 1997, 3, 561. (e) Catalano, V. J.; Parodi, N. Inorg. Chem. 1997, 36, 537. (f) Nierengarten, J.-F.; Habicher, T.; Kessinger, R.; Cardullo, F.; Diederich, F.; Gramlich, V.; Gisselbrecht, J.-P.; Boudon, C.; Gross, M. Helv. Chim. Acta 1997, 80, 2238.
41. For fullerene - dendrimer conjugates see: (a) Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J.; Wudl, F.; Srdanov, G.; Shi, S.; Li, C.; Kao, M. J. Am. Chem. Soc. 1993, 115, 9836. (b) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc., Chem. Commun. 1994, 925. (c) Camps, X.; Hirsch, A. J. Chem. Soc., Perkin Trans, 1 1997, 1595. (d) Camps, X.; Schönberger, H.; Hirsch, A. Chem. Eur. J. 1997, 3, 561. (e) Catalano, V. J.; Parodi, N. Inorg. Chem. 1997, 36, 537. (f) Nierengarten, J.-F.; Habicher, T.; Kessinger, R.; Cardullo, F.; Diederich, F.; Gramlich, V.; Gisselbrecht, J.-P.; Boudon, C.; Gross, M. Helv. Chim. Acta 1997, 80, 2238.
42. Jayaraman, N.; Nepogodiev, S. A.; Stoddart, J. F. Chem. Eur. J. 1997, 3, 1193.
43. For Langmuir films of dendrimers see for example: Saville, P. M.; Reynolds, P. A.; White, J. W.; Hawker, C. J.; Fréchet, J. M. J.; Wooley, K. L.; Penfold, J.; Webster, J. R. P. J. Phys. Chem. 1995, 99, 8283.
44. (a) Lamparth, I.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1994, 1727.
45. (b) Lamparth, I.; Schick, G.; Hirsch, A. Liebigs Ann. Red. 1997, 253.
46. (a) Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Jayaraman, N.; Nepogodiev, S. A.; Stoddart, J. F. Chem. Eur. J. 1996, 2, 1115.
47. (b) Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Jayaraman, N.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1997, 36, 732.
48. 13C NMR spectra and by mass spectrometry (fast atom bombardment for 1 and matrix-assisted laser desorption - ionization time-of-flight for 2).
49. 3) was spread on the water surface, followed by a 10 min wait for solvent evaporation before compression. The barrier was compressed at a speed of 4.0 mm/min. The amount of sample used for the UV - vis and BAM experiments is the same as that used for the isotherm experiments.
50. 2.
51. Janssen, R. A. J.; Hummelen, J. C.; Lee, K.; Pakbaz, K.; Sariciftci, N. S.; Heeger, A. J.; Wudl, F. J. Chem. Phys. 1995, 103, 788.
52. (a) Alonso, B.; Morán, M.; Casado, C. M.; Lobete, F.; Losada, J.; Cuadrado, I. Chem. Mater. 1995, 7, 1440.
53. (b) Losada, J.; Cuadrado, I.; Morán, M.; Casado, C. M.; Alonso, B.; Barranco, M. Anal. Chim. Acta 1997, 338, 191.
54. Prime, K. L.; Whitesides, G. M. Science 1997, 252, 1164.